Although Jan. 20, 1961, was a bitterly cold day in Washington, D.C., John Kennedy attended his presidential inauguration hatless. A nation of men followed suit, and soon bowlers, porkpies and fedoras were relegated to the costume cupboard of history. Kennedy killed the hat.

If it were only that simple. In fact, J.F.K. wore a black, silk top hat to his inauguration, and though he did remove it for his address, it’s more plausible that the hat died under Eisenhower’s watch. Ike’s legacy of a nationwide Interstate system meant men spent more time in cars and less time walking, waiting for trolleys and generally being outside. By 1961, hat wearers were a dying breed.

Still, that explanation implies that hats owed their ubiquity only to utility. According to Deborah Henderson, a costume designer and the author of four books about men’s headwear,
“Throughout history, people wore hats to indicate their social position in the world. Any trade — postman, engineer, pilot — had its own cap. Even lawyers, in the ’50s, all wore fedoras.”

A potent social signifier, hats identified a man’s role in society. (Hence the idiom of “putting one’s [insert profession] hat on.”) Little surprise, then, that the individualism of the ’60s and ’70s rejected the rule-bound world of hats, embracing anti-establishment
afros, flowing locks and blow-dryer-enabled atrocities. By the late ’80s, the hat stigma faded, and every couple of years since, fashion journalists proclaim the hat’s comeback. Today, hats are runway stalwarts, and classic brands—like Borsalino, Stetson and Biltmore, which until recently was based in Guelph, Ont. — are holding steady. But hats will never entirely come back. The shift is decisive: historically, men wore hats to fit in; today,
men wear hats to stand out.

My friend David Wilkinson, an investment adviser, has never minded standing out, and so I wasn’t shocked when he arrived to our annual Christmas-time Secret Scotch night (it’s like Secret Santa, but with no bad gifts) sporting a forest-green fur felt fedora. “I started
wearing a hat for warmth, but I enjoyed it so much that now I wear it everyday,” he says. Sporting a fedora on Bay Street, along with a suit and topcoat, Wilkinson says, “You get a lot of looks. You can’t be shy.”

No doubt, a hat is conspicuous. A robust sense of self-confidence is key. So too is an understanding of fit and proportion. Full-faced fellows should opt for a wide-brimmed Homburg, for instance, while others do better with slim-brimmed hats, like the fedora and the even-narrower trilby. Further, the hat should suit the outfit; brimwidth and lapel-width should harmonize. And finally, there’s the question of positioning. A hat should be slightly angled, but how low to go is a personal choice. As Henderson says, “I
have 50 historic photos of men with fedoras. Each guy wears it differently; it’s 50 identities.”